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‘Don’t worry about everything you don’t know today.’

Josh Sterling’s advice for aspiring real estate investors? Jump in head first and take massive action. In fact, if Josh could go back and offer some advice to his 17-year-old self, he would recommend skipping college and getting on the fast track to multifamily as soon as possible!

But Josh didn’t know that then, and he pursued a degree in aeronautical science from Embry-Riddle University. He got a job as a commercial airline pilot and had worked his way up to captain when the recession hit, and his hard work was rewarded with a demotion and a pay cut. Josh decided then and there that he needed a side hustle that he could control, and he landed on real estate. Josh was eventually able to quit his job and pursue real estate full-time, growing his portfolio to a cool 250 units.

Josh has also grown his business, building out his own property management team. Today he walks us through his first deals in the single-family space, discussing the challenges of managing 25 properties and how that struggle inspired his shift to multifamily. Josh offers his insight around building relationships with a few good brokers, describing how he has scaled to 250 units with the help of just two realtors. He explains his approach to multifamily syndication, sharing how multifamily allowed him to quit his job, go to work on his own terms, and have lunch with his 18-month old daughter any time he wants. Listen in for Josh’s advice about establishing credibility—with or without a track record—and getting on the fast track to multifamily.

Key Takeaways

What inspired Josh to pursue real estate

Josh’s first deal in September 2009

Why Josh made the shift to multi-family

Josh’s first multifamily deal

Josh’s next multifamily deal

Josh’s approach to raising money

Josh’s first experience with syndication

How quitting his day job changed Josh’s life

What Josh would tell his 17-year-old self

How to fast track a career as a real estate investor

What Josh is excited about right now

Josh’s advice for aspiring real estate investors

Connect with Josh

Email: [email protected]

Epic Property Management



Freddie Mac Small Balance Loan

Entrepreneurs’ Organization

Michael’s Coaching Programs

Free eBook: The Secret to Raising Money to Buy Your First Apartment Building

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